How To Get Better At Dating… Quickly

Harris O’Malley made a lot of mistakes when trying to learn how to meet women. Here he shares what he learned about dating, so you can learn it all quicker than he did.

Improving my dating life was a long, hard slog. Like most of you, I had more than my share of issues to get over – I had to let go of my Nice Guy tendencies and some deep-seated problems with being willing to accept that women were sexual beings. I also had to toss out 90% of what I thought I knew about dating and start over from scratch. But as so many people had before me, I made a lot of mistakes. I dove head-first into the pick-up scene and immediately tried to be a master PUA, with a goal of getting laid – or at least a handie in the bathroom – every night.

Considering I was coming from “Barely able to look women in the eye,” with nothing but a handful of pre-scripted lines and a head full of half-baked attraction theory, calling it ambitious would be an understatement… and frankly, it was a disaster. I had a vague idea of where I wanted to go but no idea how to get there. As a result… well, there was a lot of unintentional comedy in the first few months. The only reason why I hung on as long as I did was through sheer bloody-minded stubbornness; I was goingto master this or die trying.

It’s only in retrospect that I was able to realize that I was going about it all wrong. The will was there but my way of trying to learn was actually holding me back. And to be perfectly frank, I see people making the same mistakes I did.

So I want to help people learn from my hard-won experience. I want to show you how to get better at dating, quickly and efficiently, while avoiding all the mistakes I made.

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1) Know What You Want

On it’s face, this seems obvious: of course you want more sex, more dates, more everything… right?

Actually… not really.

In fact, this tends to be the first area where people trip themselves up. Often what you think you want is what you believe you’re supposed to want. Guys run into this all the time; we’re taught over and over again that to be a man means to want to fuck everything even vaguely hot that walks into our eyeline. If you’re in the PUA community, this narrative is reinforced constantly; you’re supposed to want a harem of the hottest girls you can find, because railing chicks is alpha, bro. Settling down is often seen as a loser’s game, getting “trapped” or “giving up”, with all the attendant jokes about eating the same meal over and over again or being restricted to just one flavor (vanilla, natch) of ice cream.

Other people have a hard time with accepting that perhaps they’re just not capable of being monogamous, or simply don’t want to follow the cultural narrative of settling down with one person and having the requisite 2.5 kids and the white picket fence. Some may be serial-monogamists at heart, or simply want no-strings attached sex with a number of friends-with-benefits.

The thing is: these are all valid options. There aren’t any wrong answers1 here. Hell, you may even find that you change over the years and what you thought you wanted was previously defined by what you thought you were your limits. You may start off wanting to experience life as a playboy and only to find that it’s not for you. You may discover that you were only monogamous because you thought that was your only option. But whether you want to be a player who has lots of casual sex or someone who finds a life-partner and settles down, you should have a clear idea in mind of just what you want, because that’s going to affect what you grow to become and the direction your life will take. You’re going to be directly controlling your personal transformation, so you want to make sure you’re becoming who you actually want to be.

While you’re at it, think of who you want – the type of women, their personalities, their archetype and where they can be found. It’s very easy to get caught up in chasing women who don’t match you either in lifestyle or interests because you think they’re what you want. Part of what held me back over the years and slowed down my progress was my focus on trying to pick up party girls at bars and clubs because they were supposed to be the hottest- barely my type when it came to just sex and definitely not my type for a relationship, whether short or long term. I’ve seen other people who get obsessed with women who are more “difficult” to pick up; strippers, bartenders, shot girls and cage dancers. Over time I came to realize I wasn’t enjoying the process – spending long periods of time in loud bars, trying to hit on women I didn’t like – and this would make it hard to even want to keep trying. I didn’t get as much from the successes and I took my failures harder than I should have. You will be far more motivated to keep up the progress if you’re spending time in places you enjoy, surrounded by people who actually want to interact with rather than just trying to get laid and not feeling particular about who it’s with.

2) Don’t Overdo It

This is the second most common mistake that people make when taking on any sort of self-improvement program: we try to go from zero to 60 without any preparation.

Dating and social skills are like exercise. You wouldn’t try to run a marathon without any prior training and expect to actually make it past the first mile. You don’t learn to swim by jumping into the deep end when you don’t even know how to dog-paddle. You don’t post up on the bench press day after day with the heaviest weights and just keep pushing until you actually shift them… not unless you like crippling injuries, that is.

When you want to bench-press, say, four hundred pounds, you don’t just strain against the bar every day until it moves. You start off building up your core muscles, working with much lighter weights and learning how to balance the bar, how to adjust your grip, how to keep your form correct so you don’t injure yourself. As you get used to the basics and build your strength, you gradually add more weight and more reps.

This was my problem; I’d read some books, taken a bootcamp and assumed that the best way for me to learn was to take a girl home every night I went out. I was greedy for results but I didn’t have any of the experience or skill to actually get them. I hadn’t spent time trying to work on the basics – just being able to hold a conversation, understanding the basis of sexual attraction or how to engage someone emotionally. I was all surface with no depth, all theory without any structure beneath it. I did improve over time… but I took a lot longer than if I’d started off working on specific skills and building my way up to trying to get laid every night. Paradoxically, taking one step at a time – starting with the smallest task and mastering it before moving on – brings about faster results than trying to take on the whole world at once.

Start with the basics – being able to talk to strangers and maintain a conversation, moving on to injecting a little banter and flirting and being more comfortable with touching – and work your way up. Not only will you progress faster, but you’ll be more motivated to keep going. Taking your time and working on your game in stages makes the whole progress less daunting than if you go out cold and try to convince a stranger to give you her phone number. Running out without preparation and practice will leave you feeling like a sexless loser when things don’t go the way you hope.

Mastering the basics will help you advance, bringing you easy wins in the beginning. And this is crucial. Those early successes will help breed more success and keep you hungry for more.

3) Practice, Practice, Practice

The way you get better at any skill is through practice… and you should be practicing all the time.

We tend to compartmentalize dating off from our everyday lives, as though it were a part of us that we can turn on or off… but it’s not. Getting better at dating isn’t just about going out three nights a week and making at least ten approaches a night, it’s about your entire life. Learning how to be a better, more attractive person requires a holistic approach that incorporates everyaspect of your lifestyle. The skills involved in approaching strangers at bars are the same ones you use to network with others for your job – the only difference are your end-goals. The better you are at engaging with people in general, the better you will be at charming others into your bed.

During the day, you want to make a point of working on your basic skills; this is your time to start patching over rough spots and overcoming sticking points. If, for example, you’re still having a hard time with approach anxiety, then you want to make a point to go up to strangers and start talking – just asking for the time or directions at first, then building up to being able to hold a brief conversation before moving on. If you’re having a hard time connecting with people, then you want to work on being more engaging – being able to stay in a conversation longer without overstaying your welcome. Everywhere you go is an opportunity to practice – standing in line at Starbucks, the produce aisle at Trader Joe’s, the warm-up period before your Krav Maga class. If your day consists of going to work and going home with minimal interaction with the outside world in between, then you need to deliberately go out and actually take part in the world around you; you aren’t going to improve at social skills without actually being social.

While the days are for practicing the basics, then the nights are for rehersal – you want to go out and practice without feeling like there are consequences for failure. Pick at least three nights a month to go out specifically to work putting your skills together; you want to go out some place with the specific purpose to approach people without the expectation of success. Your goal simply is to experiment and get used to the mechanics of actually approaching and flirting with people, to identify weaknesses and try new methods and techniques.

There’s a saying in pick-up that I actually like: the first 1000 approaches don’t count. The idea is that during those first thousand approaches, you have no idea what you’re doing – you’re still stumbling around, working out the mechanics of everything you’ve learned and putting them into practice. So you need to give yourself permission to fail; you’re not out to get numbers or dates, you’re simply trying new things. If you get a date, great. If you get shot down, it doesn’t count; it’s just another step on the path to mastery.

4) Document Everything

One of the easiest ways to get frustrated with any sort of self-improvement regimen is to feel like you’re not making any progress. When you feel like Sisyphus constantly rolling the rock uphill and getting nowhere, then you’re going to end up being demoralized quickly and give up.

Sometimes it’s very easy to lose track of just how far you’ve actually come versus where you think you are. We tend to get tunnel vision and focusing on one specific goal – getting same night lays, for example – and ignore or disregard all of the progress we’ve made up until that point. Sure, you may not be pulling new girls home every night of the week, but when you’ve gone from barely being able to stammer “hello” to consistently getting phone numbers and setting up dates, you’ve made amazing progress.

Other times you may get stuck on a specific issue without being aware of it. You may consistently be violating somebody’s personal space, forgetting to actually touch the people you’re talking to or simply letting conversations roll on too long without establishing that yes, you’re interested in them as more than just a potential Bridge partner.

The way to help identify these issues is to check your metrics – and the only way to do that is to write everything down. I’m a big believer in journaling one’s progress; it’s an easy way of measuring your improvement, tracking how close you’re coming to new milestones or identifying patterns of behavior and areas that you need to work on.

The exact method of documentation will vary depending according to your personality. Some people – like me – do better with taking a more narrative approach and writing actual journal entries. Others will find more use out of sticking to raw data and numbers, using spreadsheets and graphs to chart their progress. Regardless of your method however, you want to include as much information as possible – what you wore, where you stood, how you felt, what you said, what they said, how many approaches you’d made that day, how much you had to drink. Sometimes the answers lie in the smallest details; one of my problems was that I found I was over-relying on booze to power past my initial approach anxiety. It was only when I noticed a correlation between my levels of success and how many beers I’d had that night that I realized that by my sixth approach, I’d passed from “loosened up” to “actually drunk” and was missing crucial social cues. By limiting the number of drinks for the evening and spending more time addressing my nervousness through controlling my breathing and following the three-second rule, I was able to finally get over that particular hurdle.

At the end of each week, be sure to take time and read over your notes; not only will it give you a fresh perspective, but it will help remind you of just how far you’ve come.

5) Welcome Plateaus

As you start off, you’re going to have some quick early successes and rapid improvement; this is exactly how you want things to go – after all, success breeds success and those early wins are critical to staying motivated. However, as you get better at dating, you are inevitably going to plateau out and all that improvement is going to come to a screeching halt. Suddenly it seems like no matter what you do, you just can’t seem to make any forward progress. You’ll feel like you’re doing something wrong, like you’re losing ground and in danger of sliding back into the bad old days.

Except… you’re wrong. Believe it or not – this is a good thing. You see, hitting a plateau is a sign of just how much you’ve improved. It’s a sign that you’ve reached a new level of mastery.

You see, the better you get at something, the more effort it takes to improve. You improve quickly at the start because you’ve been learning the basics, getting the underlying structure of the changes you want to make. But once you master them, it becomes time to build on them and fine-tune them; the more you learn, the more you realize just how much more there is that you never realized before. A white belt in karate is learning the stances and the forms that build the foundation of the martial art; a black belt is learning the control it takes to make them fluid and seemingly effortless.

Now I get that it’s frustrating; after such rapid growth, you want to keep progressing at the same rate. But those plateaus are where the real opportunities for improvement come in. The key to getting past a plateau is keep moving forward. Just as mastering a tricky maneuver in akata requires practicing it over and over again until it becomes second nature, you want to knuckle down and practice your social skills constantly.

This may mean going out and changing up your technique, finding new ways to bring your personality into your particular style of attraction and banter. Give yourself challenges. Go out and fuck up deliberately to practice recovering from mistakes. Spend time pushing your limits and approaching people you think you could never get with. Find your sticking points and drill them over and over again until they become new strengths.

Just whatever you do: don’t give up. Welcome those plateaus; they’re the opportunity to reach new levels of success. And with every new level, you come even closer to achieving things you never believed were possible.

About Harris O'Malley

Harris O'Malley provides geek dating advice at his blog Paging Dr. NerdLove, as well as writing the occasional guest review for Spill.com and appearing on the podcast The League of Extremely Ordinary Gentlemen. He can be found dispensing snark and advice on Facebook and Twitter (@DrNerdLove.)

Dr. NerdLove is not really a doctor.

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